James and Nell met during their first week at Epic Systems, when James sat down next to Nell during a new hire orientation class. Nell gave James her number for 4th of July plans, but James lost it and had to hunt Nell down for it again later after the 4th. The two quickly became close friends, bonding over golf and baseball. They followed Nell's Red Sox through the playoffs that year - their first official date was a trip to St. Louis for game 3 of the World Series. The Sox lost the game, but won the series. James' original proposal plans were delayed by the pandemic. He asked Nell for her hand amongst the beautiful fall colors of the University of Wisconsin Arboretum in October 2020.